With great thermal and chemical stabilities, spiro compounds with 9,9′-spirobifluorene core of inherent rigid structure have attracted great attention as organic functional materials.
Structurally, 9,9′-Spirobifluorene (SBF) can be considered as two fluorenes joined together at 9,9'-positions. 9,9'-Spirobifluorene has received considerable interest for organic electronics, featuring a sp3-hybridized carbon with two perpendicularly aligned π systems. The two fluorene units through a shared spiro-carbon are hence maintained in orthogonal planes.
Spiro compounds with 9,9′-spirobifluorene core of inherent rigid structure thus have attracted great attention as organic functional materials for their specific physical properties, such as high glass transition temperatures, good solubility and their amorphous nature. The prominent spiro-structure can also very effectively suppresses excimer formation frequently observed in the solid state of many fluorescent dyes. Particularly, spirobifluorenes are known for their excellent thermal and chemical stabilities, high quantum efficiencies, as well as nondispersive ambipolar carrier transporting properties.
9,9'-spirobifluorene-based conjugated microporous organic polymers (COPs) can be obtained directly from unsubstituted spirobifluorene using an inexpensive FeCl3 mediator via either oxidative polymerization, Friedel-Crafts polymerization, or competitive oxidative/Friedel-Crafts polymerization. Those COPs show large surface areas (940–1980 m2 g-1) and high micropore volumes (0.5–0.9 cm3 g-1).
|Molecular weight||316.39 g/mol|
|Classification / Family||Spirobifluorene, semiconductor synthesis intermediates, low band gap polymers, OLED, OFETs, organic photovoltaics|
|Melting point||Tm = 202 °C|
Literature and Reviews
Hole Mobilities of 2,7- and 2,2′-Disubstituted 9,9′-Spirobifluorene-Based Triaryldiamines and Their Application as Hole Transport Materials in OLEDs, Y. Liao et al., Chem. Mater. , 19, 6350–6357 (2007); DOI: 10.1021/cm702230.
- 2-Substituted vs 4-substituted-9,90-spirobifluorene host materials for green and blue phosphorescent OLEDs: a structureeproperty relationship study, S. Thiery et al., Tetrahedorn, 70, 6337-6351 (2014); DOI: 10.1016/j.tet.2014.05.081.
- Synthesis, Structures, and Photoinduced Electron Transfer Reaction in the 9,9′-Spirobifluorene-Bridged Bipolar Systems, K. Wong et al., J. Org. Chem. 2006, 71, 456-465 (2006); DOI: 10.1021/jo0512047.
- Fluorinated 9,9′-spirobifluorene derivatives as host materials for highly efficient blue organic light-emitting devices, Z. Li et al., J. Mater. Chem. C, 1, 2183-2192 (2013); 10.1039/C3TC00466J.
- White organic light-emitting diodes based on 2,7-bis(2,2-diphenylvinyl)-9,9′-spirobifluorene: Improvement in operational lifetime, C. Chuen et al., Appl. Phys. Lett., 85, 4609 (2004); DOI: 10.1063/1.1824178.
- Bis(diphenylamino)-9,9′-spirobifluorene functionalized Ir(iii) complex: a conceptual design en route to a three-in-one system possessing emitting core and electron and hole transport peripherals, H. Chen et al.,J. Mater. Chem., 21, 768-774 (2011); DOI: 10.1039/C0JM02097D.
- 9,9′-Spirobifluorene and 4-phenyl-9,9′-spirobifluorene: pure hydrocarbon small molecules as hosts for efficient green and blue PhOLEDs, S. Thiery et al., J. Mater. Chem. C, 2, 4156-4166 (2014); DOI: 10.1039/C4TC00171K.
- Synthesis of 9,9'-Spirobifluorene-Based Conjugated Microporous Polymers by FeCl3-mediated Polymerization, A. Modak et al., Polym. Chem., 7, 1290-1296 (2016); 10.1039/C5PY01900A.
- Highly efficient and stable organic light-emitting diode using 4,4′-bis(N-carbazolyl)-9,9′-spirobifluorene as a thermally stable host material, T. Tsuzuki et al., Appl. Phys. Lett., 94, 033302 (2009); DOI: 10.1063/1.3073709.
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